I am willing to bet a year's pay that Barbara Gaines Winkelman is the only Chestnut Hill resident who has ever been a guest on David Letterman's long-running late night TV show. (Letterman hosted Late Night with David Letterman on NBC from 1982 to 1993 and the Late Show with David Letterman on CBS from 1993 to  2015.)

Winkelman, 60, who writes the occasional Citizen Canine feature in the Local about fascinating local dogs and their owners, is a Long Island native, University of Pennsylvania graduate (1983, English major), law school graduate, former editor of a legal publication and author of 15 books for children, but those accomplishments, as impressive as they are, are not the reasons she was talking to David Letterman on national TV.

“I happened to see an article in Rolling Stone magazine in the 1980s about Letterman's staff,” explained the local dog lover. “I noticed that there was a production assistant on the staff named Barbara Gaines, which was my maiden name. It turned out that her last name had been changed years before from Ginsburg, and so was mine. This fascinated me, so I wrote a letter to her. One year later she wrote back to me. They found my name in the phone book under Barbara Gaines. 

“The next day I got a call from the show asking me to come on. I was in law school at the time. There was a third Barbara Gaines from Chicago who was also asked to come on, but she couldn't make it. I was on the show with (Hollywood actor) Don Ameche. I told the producer about a phone call I had gotten saying 'You f--- b---. You stole my boyfriend!' Obviously, that call was meant for someone else. The producer told me to say that on the show and use that exact language, so I did. The curse words were bleeped out. David acted like he was very offended by the language, and (music director) Paul Shaffer wrote a song comparing the two Barbara Gaines. It was in 1985, and I was told that it is now on YouTube.”

A native of Long Island, Barbara came to Philadelphia as a student at Penn. (Her father was a dentist, and her mother was a teacher. Two of her siblings are medical doctors, and a third is a learning specialist.) She then worked in the accounting department of a New York law firm for two years, then went to law school at Yeshiva University. She worked in divorce law and elderly law for a general practice firm in Connecticut for three years, then decided that a career in the law was not for her, after all. “When I was deciding on a career,” said Barbara, “I did not think it through well enough.”

Barbara became the editor of an American Lawyers Management Services periodical, which later folded, but a friend, Katherine Tegin, asked her to edit children's books for Hyperion, which produces Disney-related publications “I started writing text for one because the illustrator wasn't doing much of that. Katherine liked it and said I should be writing children's books. She wanted to start a new series using Winnie the Pooh characters. So many bosses are not generous, but she certainly was.”

Barbara's first children's book was “Pooh's Pumpkin” in 1995. (Disney owns the rights to the Pooh characters.) Its success prompted her to do 11 more Winnie the Pooh books, then one about a Disney World ride and three for Grolier, an educational publishing company. 

Winkelman was 42 when she wrote her last book. Her husband, Billy, a U of P Wharton School graduate and East Falls native, got a management job with Starbucks, so the couple moved to Seattle in 1998. He developed the “Starbucks card” and later worked for Microsoft. Now he is a career counselor. They married in 1988 and lived in Westport, CT, before going to Seattle, where they lived for 20 years. In 2018 they came back to Philly by driving 3000 miles because they did not want to put their dog, a Westie named Lucy, on a plane. (Now they have a Poodle/Bichon mix, Ruth Bader Puppy.) In 2003 Barbara earned a master's degree in teaching at Seattle University and taught writing in the Seattle area for 10 years. 

They couple came back to Philly because all of their family members live on the east coast. They have two children, A.J., 28, and Hannah, 25 Barbara also has a blog, “Warning: No Spoilers!” 

Len Lear can be reached at lenlear@chestnuthilllocal.com